(3R,4R,5S)-3,4,5,6-Tetrahydroxy-2-oxo-hexanoic acid methyl ester | 1071558-27-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3R,4R,5S)-3,4,5,6-Tetrahydroxy-2-oxo-hexanoic acid methyl ester
• 英文别名: L-lyxo-[2]hexulosonic acid methyl ester；L-lyxo-[2]Hexulosonsaeure-methylester；methyl 2-keto-L-gulonate；methyl 2-ketogulonate；methyl (3R,4R,5S)-3,4,5,6-tetrahydroxy-2-oxohexanoate
• CAS: 1071558-27-4
• 化学式: C₇H₁₂O₇
• 分子量: 208.168
• InChiKey: KPHIBLNUVRGOGU-VPENINKCSA-N

物化性质

• 熔点：
  138-139 °C
• 沸点：
  495.4±45.0 °C(Predicted)
• 密度：
  1.532±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.5
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  124
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (3R,4R,5S)-3,4,5,6-Tetrahydroxy-2-oxo-hexanoic acid methyl ester 在 sodium carbonate 作用下， 以 甲醇 为溶剂， 生成 sodium ascorbate
  参考文献：
  名称：

  Method of making ascorbyl monophosphates

  摘要：

  本发明提供了一种制备L-抗坏血酸2-磷酸盐的碱金属和碱土金属盐的方法，包括在浓缩水溶液中，在碱性条件下将L-抗坏血酸2-多磷酸与L-抗坏血酸的碱金属或碱土金属盐反应。L-抗坏血酸盐的量超过多磷酸的摩尔量，反应介质的pH值保持在约8到约11的范围内，直到大部分多磷酸被消耗，只有L-抗坏血酸2-磷酸盐存在。本发明的另一个方面包括在反应完成后将得到的混合物喷雾干燥，冷却和稀释至适当的粘度。根据本发明的处理产物适用于人类和动物食品的添加剂；它特别稳定，不易氧化和热降解，并且L-抗坏血酸磷酸盐的含量特别高，相对于多磷酸，因此主要用于鱼类饲料的营养强化。

  公开号：

  US06063937A1
• 作为产物：
  描述：

  sodium ascorbate 以 甲醇 为溶剂， 生成 (3R,4R,5S)-3,4,5,6-Tetrahydroxy-2-oxo-hexanoic acid methyl ester
  参考文献：
  名称：

  Solvent exchange process

  摘要：

  一种回收有机酸或其金属盐的工艺包括将含有一种或多种有机酸或其金属盐的醇相与水接触，在有效条件下提供含有部分有机酸或其金属盐的水相。水相不含有大量的醇。该工艺还可以包括从水相中回收有机酸或其金属盐。

  公开号：

  US06320061B1

文献信息

• Ascorbic acid process
  申请人：Pfizer Inc.

  公开号：US04180511A1

  公开（公告）日：1979-12-25

  An improved process for the preparation of ascorbic acid and erythorbic acid is disclosed, the improvement comprising the removal of borate impurities from a 2-ketogulonate and a 2-ketogluconate prior to formation of the desired acids by base catalyzed cyclization.

  揭示了一种改进的制备抗坏血酸和鼠李糖酸的工艺，该改进包括在通过碱催化环化形成所需酸之前，从2-酮戊糖酸和2-酮葡萄糖酸中去除硼酸杂质。
• Ascorbic acid synthesis
  申请人：Pfizer Inc.

  公开号：US04111958A1

  公开（公告）日：1978-09-05

  Ascorbic acid is prepared from a 1,4-lactone selected from gulono-1,4-lactone, galactono-1,4-lactone, idono-1,4-lactone and talono-1,4-lactone by a process comprising protection of the hydroxyl groups of the lactone so as to form an intermediate having a free hydroxyl group at either, but not both, the 2- or 3-position, oxidizing this free hydroxyl group to a keto group and hydrolyzing the oxidized intermediate to remove the hydroxyl-protecting groups.

  抗坏血酸是从古洛酮-1,4-内酯、半乳糖酮-1,4-内酯、异戊糖酮-1,4-内酯和他戊糖酮-1,4-内酯中选择的一种1,4-内酯制备而成，其过程包括保护内酯的羟基，以形成一个中间体，在2-或3-位置之一具有一个自由羟基，然后将这个自由羟基氧化为酮基，最后水解氧化的中间体以去除羟基保护基团。
• Reduction of 2,5-diketogluconic acid
  申请人：Pfizer Inc.

  公开号：US04159990A1

  公开（公告）日：1979-07-03

  The novel stereoselective and regioselective alkali metal borohydride reduction of 2,5-diketogluconic acid, alkyl esters or salts thereof to form 2-ketogulonic acid together with lesser amounts of 2-ketogluconic acid is disclosed. The 2-ketogulonic acid is readily converted to ascorbic acid.

  本发明揭示了2,5-二酮葡糖酸，烷基酯或盐的立体选择性和区域选择性碱金属硼氢化物还原，以形成2-酮戊糖酸以及较少量的2-酮葡萄糖酸。 2-酮戊糖酸可以轻松转化为抗坏血酸。
• Preparation of 2-ketogulonic acid
  申请人：Pfizer Inc.

  公开号：US04212988A1

  公开（公告）日：1980-07-15

  2,5-Diketogluconic acid, alkyl esters or salts thereof, are reduced by an amine-borane to 2-ketogulonic acid, an intermediate for the preparation of ascorbic acid.

  2,5-二酮戊糖酸，其烷基酯或盐，通过氨硼烷还原为2-酮戊糖酸，这是制备抗坏血酸的中间体。
• Bench to Bedside Resuscitation from Prolonged Ventricular Fibrillation
  作者：Mark G. Angelos、James J. Menegazzi、Clifton W. Callaway

  DOI：10.1111/j.1553-2712.2001.tb01155.x

  日期：2001.9

  AbstractVentricular fibrillation (VF) remains the most common cardiac arrest heart rhythm. Defibrillation is the primary treatment and is very effective if delivered early within a few minutes of onset of VF. However, successful treatment of VF becomes increasingly more difficult when the duration of VF exceeds 4 minutes. Classically, successful cardiac arrest resuscitation has been thought of as simply achieving restoration of spontaneous circulation (ROSC). However, this traditional approach fails to consider the high early post—cardiac arrest mortality and morbidity and ignores the reperfusion injuries, which are manifest in the heart and brain. More recently, resuscitation from cardiac arrest has been divided into two phases; phase I, achieving ROSC, and phase II, treatment of reperfusion injury. The focus in both phases of resuscitation remains the heart and brain, as prolonged VF remains primarily a two‐organ disease. These two organs are most sensitive to oxygen and substrate deprivation and account for the vast majority of early post‐resuscitation mortality and morbidity. This review focuses first on the initial resuscitation (achieving ROSC) and then on the reperfusion issues affecting the heart and brain.